Methyl Isocyanate → 4-(2-Hydroxybenzylideneamino)naphth-1-yl methylcarbamate

HRID 434721

反応式

HRID 434721 の反応式
[OH:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH:4]=[N:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([OH:16])=[CH:8][CH:7]=1.[CH3:21][N:22]=[C:23]=[O:24]>C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.O1CCCC1>[CH3:21][NH:22][C:23](=[O:24])[O:16][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([N:5]=[CH:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=2[OH:1])=[CH:7][CH:8]=1

参加物

5

反応物 2

HCID 12228Methyl IsocyanateHCID 1356896084-(2-Hydroxybenzylideneamino)-1-naphthol

生成物 1

HCID 1356896174-(2-Hydroxybenzylideneamino)naphth-1-yl methylcarbamate収率 100%

試薬・触媒・溶媒 2

HCID 9798523Di-n-butyl diacetoxy tin触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a 350 milliliter glass pressure bottle equipped with a magnetic stirrer was added 4.00 grams (0.015 moles) of 4-(2-hydroxybenzylideneamino)-1-naphthol prepared in Part A, 1.03 grams (0.018 moles) of methyl isocyanate, 100 milliliters of tetrahydrofuran and 5 drops of dibutyl tin diacetate. The resulting reaction mixture was stirred for 18 hours at room temperature after which the volatiles were removed under reduced pressure and the remaining residue dissolved in ether. The ethereal solution was washed twice with a 1% aqueous sodium bicarbonate solution and twice with a saturated brine solution, dried over magnesium sulfate and concentrated under reduced pressure to give 4.87 grams (0.015 moles) of 4-(2-hydroxybenzylideneamino)naphth-1-yl methylcarbamate in the form of a pale yellow solid having a melting point of 143°-145.5° C. and the following structural formula: ##STR16##

後処理

  1. customThe resulting reaction mixture
  2. customwere removed under reduced pressure
  3. dissolutionthe remaining residue dissolved in ether
  4. washThe ethereal solution was washed twice with a 1% aqueous sodium bicarbonate solution and twice with a saturated brine solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-877c77b0d6394bb6abe197c36150f87d
出典データセット
uspto-grants-1983_08
特許番号
US04399148

関連ノート

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